How to Find Trusted Advisors as a Business Owner
There’s a specific kind of conversation that most business owners need and almost none of them have regularly. Not a strategy session. Not a coaching call. Not a board meeting. Something more honest than any of those, with someone who has no stake in the outcome and no reason to tell you what you want to hear.
Finding that person, or those people, is one of the most underrated things a growing business owner can do. And most founders wait too long to start looking.
Why the People Around You Can’t Always Be the People You Talk To
The closest people in a CEO’s life are often the least equipped to give them what they actually need in hard moments. Not because they don’t care, but because the relationship makes full honesty complicated.
Employees can’t tell you the hard truth without risking their job, even in a culture where psychological safety exists. That’s not a failure of the culture. It’s a structural reality. The power dynamic doesn’t go away just because you’ve told people it’s safe to speak up.
Family members are invested in a different way. They want you to be okay. They don’t always want the full picture of what’s going wrong, and you don’t always want to give it to them. Protecting the people you love from unnecessary worry is reasonable. But it means you’re carrying things alone.
Krista Crawford, a Vistage chair who works closely with founders and executives, described this directly in a recent episode of recent episode of The Fast Slow Motion Podcast. Who is going to give a CEO a hard truth other than another CEO? The answer, most of the time, is no one. Unless you build for it.
What a Trusted Advisor Actually Looks Like
The phrase trusted advisor gets used loosely. A banker, an accountant, an attorney — those people can be valuable, but they’re usually advising on their area of expertise, and their relationship with you comes with its own dynamics.
What Krista describes is something different. A trusted advisor in this context is someone outside your business and outside your family who knows you well enough to be honest with you, cares enough to do it carefully, and has no financial stake in the advice they give.
The specific qualities matter. They’re not going to see you through a negative lens. They’re going to assume you’re trying to do the right thing and engage with you from that assumption. They’ll give you honest feedback and expect the same from you when they need it. That reciprocity is part of what makes the relationship work.
This kind of advisor often comes from a peer group, a former colleague relationship that’s developed over time, or a community built around a shared professional context. It rarely comes from a formal introduction or a professional services referral.
The Case for Peer Groups
The most reliable structure for finding trusted advisors at scale is a peer group. Not because every group will deliver what Krista describes, but because the best ones are specifically designed to create the conditions for it.
In a well-run peer group, the room is confidential. What gets said there doesn’t leave. The people in it are peers, meaning they understand what it actually feels like to be in your position. They’ve made decisions you’re about to make. They’ve failed in ways that are relevant to your situation. And they have no reason to tell you what you want to hear.
Krista estimates that about 40% of what gets discussed in her Vistage groups is personal. A health scare. A difficult family situation. Something that’s affecting focus and performance in ways that don’t show up in a metrics review. The peer group is one of the few places where a CEO can bring that without it creating downstream complications.
The other thing a good peer group provides is resources. The people in the room know attorneys, CPAs, advisors, and specialists in your geographic area. They’ve used them, evaluated them, and can give you a real opinion. That’s a different kind of value than a Google search or a professional directory.
How to Evaluate Whether a Group Is Actually Worth Your Time
Not every peer group delivers what it promises. Some are networking events with a structured agenda. Others are built around content delivery more than peer conversation. What you’re looking for is a group where the culture prioritizes honesty, the facilitation is strong, and the members are at a similar stage and scale.
A few things worth looking for. Is there genuine confidentiality, enforced by structure and not just norms? Are the members willing to share things that are actually hard, or does the conversation stay surface-level? Does the chair or facilitator model the kind of honesty they’re asking for from the group? Do you leave the meetings with something you couldn’t have gotten anywhere else?
If the answer to most of those is yes, you’ve found something worth protecting on your calendar. If the answer is mostly no, it’s worth looking for a different group rather than concluding that peer groups don’t work.
Building One-on-One Relationships That Fill the Same Need
A peer group is the most efficient structure for this, but it’s not the only one. Some business owners build what they need through a small number of individual relationships with other founders or executives they trust.
These relationships tend to develop over time rather than by design. A former colleague who started their own company. Someone you met in a professional context who turned out to be unusually direct and thoughtful. A person from a past peer group that dissolved but whose relationship you kept.
The key is that the relationship has to be reciprocal. You’re not looking for a mentor who gives and gives. You’re looking for someone who will tell you the hard thing when you need to hear it, and who trusts you to do the same for them. That kind of relationship requires investment from both sides, and it requires you to actually show up honestly when it’s your turn to receive feedback.
Start Before You Think You Need It
The time to build this network is not when you’re in crisis. By the time you’re underwater, the relationships that could help you most take time to develop that you don’t have.
The business owners who navigate the hard chapters best are almost always the ones who built the relationships before they needed them. They weren’t looking for a lifeline. They were investing in connection that happened to be there when the hard moment arrived.
That’s the real argument for finding trusted advisors now, not later. Not because something is wrong, but because at some point, something will be. And when it is, having people who know you, who will tell you the truth, and who have been there themselves is worth more than almost anything else you could have built.
Listen to the full podcast episode here.